Bakuchiol

Modify Date: 2024-01-02 11:45:45

Bakuchiol structure	Common Name	Bakuchiol
	CAS Number	10309-37-2	Molecular Weight	256.383
	Density	1.0±0.1 g/cm3	Boiling Point	391.4±21.0 °C at 760 mmHg
	Molecular Formula	C₁₈H₂₄O	Melting Point	N/A
	MSDS	Chinese USA	Flash Point	176.6±11.7 °C

Use of Bakuchiol

Bakuchiol is a phytoestrogen isolated from the seeds of Psoralea corylifolia L; has anti-tumor effects.IC50 value:Target:in vitro: Bakuchiol reduced mitochondrial membrane potential (Psim) of cells in a concentration- and time-dependent manner, showing a more potent effect than that of resveratrol. S phase arrest, caspase 9/3 activaton, p53 and Bax up-regulation, as well as Bcl-2 down-regulation were observed in bakuchiol-treated A549 cells [1]. UGT2B7 was inhibited by the strongest intensity. The noncompetitive inhibition was demonstrated by the results obtained from Dixon plot and Lineweaver-Burk plot. The Ki value was calculated to be 10.7 μM [2]. Bakuchiol was found to be naturally occurring potent inhibitors of hCE2, with low Ki values ranging from 0.62μM to 3.89μM [3]. After exposure to bakuchiol at 0.25-fold, 0.5-fold and 1-fold of minimum inhibitory concentration (MIC) (3.91 μg/ml) for 24h, the fungal conidia of T. mentagrophytes demonstrated a significant dose-dependent increase in membrane permeability. Moreover, bakuchiol at 1-fold MIC elicited a 187% elevation in reactive oxygen species (ROS) level in fungal cells after a 3-h incubation [4].in vivo: In combination with the reported concentration after an intravenous administration of bakuchiol (15 mg/kg) in rats, the high risk of in vivo inhibition of bakuchiol towards UGT2B7-catalyzed metabolism of drugs was indicated [2]. In a guinea pig model of tinea pedis, bakuchiol at 1%, 5% or 10% (w/w) concentration in aqueous cream could significantly reduce the fungal burden of infected feet (p<0.01-0.05) [4].

Name	4-(3,7-Dimethyl-3-vinylocta-1,6-dien-1-yl)phenol
Synonym	More Synonyms

Description	Bakuchiol is a phytoestrogen isolated from the seeds of Psoralea corylifolia L; has anti-tumor effects.IC50 value:Target:in vitro: Bakuchiol reduced mitochondrial membrane potential (Psim) of cells in a concentration- and time-dependent manner, showing a more potent effect than that of resveratrol. S phase arrest, caspase 9/3 activaton, p53 and Bax up-regulation, as well as Bcl-2 down-regulation were observed in bakuchiol-treated A549 cells [1]. UGT2B7 was inhibited by the strongest intensity. The noncompetitive inhibition was demonstrated by the results obtained from Dixon plot and Lineweaver-Burk plot. The Ki value was calculated to be 10.7 μM [2]. Bakuchiol was found to be naturally occurring potent inhibitors of hCE2, with low Ki values ranging from 0.62μM to 3.89μM [3]. After exposure to bakuchiol at 0.25-fold, 0.5-fold and 1-fold of minimum inhibitory concentration (MIC) (3.91 μg/ml) for 24h, the fungal conidia of T. mentagrophytes demonstrated a significant dose-dependent increase in membrane permeability. Moreover, bakuchiol at 1-fold MIC elicited a 187% elevation in reactive oxygen species (ROS) level in fungal cells after a 3-h incubation [4].in vivo: In combination with the reported concentration after an intravenous administration of bakuchiol (15 mg/kg) in rats, the high risk of in vivo inhibition of bakuchiol towards UGT2B7-catalyzed metabolism of drugs was indicated [2]. In a guinea pig model of tinea pedis, bakuchiol at 1%, 5% or 10% (w/w) concentration in aqueous cream could significantly reduce the fungal burden of infected feet (p<0.01-0.05) [4].
Related Catalog	Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK Research Areas >> Cancer Natural Products >> Terpenoids and Glycosides
References	[1]. Chen Z, et al. Anti-tumor effects of bakuchiol, an analogue of resveratrol, on human lung adenocarcinoma A549 cell line. Eur J Pharmacol. 2010 Sep 25;643(2-3):170-9. [2]. Xu Y, et al. In vitro evidence for bakuchiol's influence towards drug metabolism through inhibition of UDP-glucuronosyltransferase (UGT) 2B7. Afr Health Sci. 2014 Sep;14(3):564-9. [3]. Li YG, et al. Fructus Psoraleae contains natural compounds with potent inhibitory effects towards human carboxylesterase 2. Fitoterapia. 2015 Jan 13;101C:99-106. [4]. Lau KM, et al. Anti-dermatophytic activity of bakuchiol: in vitro mechanistic studies and in vivo tinea pedis-inhibiting activity in a guinea pig model. Phytomedicine. 2014 Jun 15;21(7):942-5.

Description

Related Catalog

Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK

Research Areas >> Cancer

Natural Products >> Terpenoids and Glycosides

References

[1]. Chen Z, et al. Anti-tumor effects of bakuchiol, an analogue of resveratrol, on human lung adenocarcinoma A549 cell line. Eur J Pharmacol. 2010 Sep 25;643(2-3):170-9.

[2]. Xu Y, et al. In vitro evidence for bakuchiol's influence towards drug metabolism through inhibition of UDP-glucuronosyltransferase (UGT) 2B7. Afr Health Sci. 2014 Sep;14(3):564-9.

[3]. Li YG, et al. Fructus Psoraleae contains natural compounds with potent inhibitory effects towards human carboxylesterase 2. Fitoterapia. 2015 Jan 13;101C:99-106.

[4]. Lau KM, et al. Anti-dermatophytic activity of bakuchiol: in vitro mechanistic studies and in vivo tinea pedis-inhibiting activity in a guinea pig model. Phytomedicine. 2014 Jun 15;21(7):942-5.

Density	1.0±0.1 g/cm3
Boiling Point	391.4±21.0 °C at 760 mmHg
Molecular Formula	C₁₈H₂₄O
Molecular Weight	256.383
Flash Point	176.6±11.7 °C
Exact Mass	256.182709
PSA	20.23000
LogP	6.40
Vapour Pressure	0.0±0.9 mmHg at 25°C
Index of Refraction	1.555

Bakuchiol MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: SL3785000

CHEMICAL NAME :: Phenol, 4-(3-ethenyl-3,7-dimethyl-1,6-octadienyl)-, (S-(E))-

CAS REGISTRY NUMBER :: 10309-37-2

LAST UPDATED :: 199801

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C18-H24-O

MOLECULAR WEIGHT :: 256.42

WISWESSER LINE NOTATION :: QR D1U1X1&1U1&3UY1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: MZHUDX Mikrobiologicheskii Zhurnal (Kiev). Journal of Microbiology. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.40- 1978- Volume(issue)/page/year: 42,646,1980

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2560 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: MZHUDX Mikrobiologicheskii Zhurnal (Kiev). Journal of Microbiology. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.40- 1978- Volume(issue)/page/year: 42,646,1980

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 94 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: MZHUDX Mikrobiologicheskii Zhurnal (Kiev). Journal of Microbiology. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.40- 1978- Volume(issue)/page/year: 42,646,1980

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 31 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: MZHUDX Mikrobiologicheskii Zhurnal (Kiev). Journal of Microbiology. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.40- 1978- Volume(issue)/page/year: 42,646,1980 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2500 mg/kg/10D-I

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

REFERENCE :: MZHUDX Mikrobiologicheskii Zhurnal (Kiev). Journal of Microbiology. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.40- 1978- Volume(issue)/page/year: 42,646,1980

Hazard Codes	F+
RIDADR	NONH for all modes of transport
RTECS	SL3785000
HS Code	2907199090

HS Code	2907199090
Summary	2907199090 other monophenols VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

Bakuchiol derivatives as novel and potent cytotoxic agents: a report.

Eur. J. Med. Chem. 49C , 55-67, (2012)

A library of 28 compounds comprising of acyl, amino, halo, nitro, styryl and cyclized derivatives of bakuchiol have been evaluated against a panel of eight human cancer cell lines. Bioevaluation studi...

Phenolic compounds isolated from Psoralea corylifolia inhibit IL-6-induced STAT3 activation.

Planta Med. 78(9) , 903-6, (2012)

Inhibiting interleukin-6 (IL-6) has been postulated as an effective therapy in the pathogenesis of several inflammatory diseases. In this study, seven flavonoids were isolated from the methanol extrac...

Chemical fingerprint and quantitative analysis of fructus psoraleae by high-performance liquid chromatography.

J. Sep. Sci. 30(6) , 813-8, (2007)

Fructus Psoraleae, a widely used traditional Chinese medicine, is well known as a health supplement ingredient. In our study, an improved and comprehensive HPLC fingerprint of Fructus Psoraleae was es...

P-(3,7-dimethyl-3-vinylocta-trans-1,6-dimethyl) phenol

Phenol, 4-[(1E,3S)-3-ethenyl-3,7-dimethyl-1,6-octadien-1-yl]-

BACTRIS GASIPAES FRUIT JUICE

4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dien-1-yl]phenol

Backuchiol

Bakuchiol

4-[(1E,3S)-3,7-Dimethyl-3-vinyl-1,6-octadien-1-yl]phenol

Drupanol

4-[(1E,3S)-3,7-Dimethyl-3-vinylocta-1,6-dien-1-yl]phenol

(S)-bakuchiol

UP 256

Phenol, 4-[(1E,3S)-3-ethenyl-3,7-dimethyl-1,6-octadienyl]-

BioBioPha
China
Product Name: Bakuchiol
Price: ￥Inquiry/20mg
Purity: 98.0%
Stocking Period: 1 Day
Contact: Xueping-Zheng

Shanghai Jizhi Biochemical Technology Co., Ltd
China
Product Name: Bakuchiol
Price: ￥588.0/20mg
Purity: 98.0%
Stocking Period: 2 Day
Contact: Liu jia

DC Chemicals Limited
China
Product Name: Bakuchiol
Price: $280.0/20mg
Purity: 98.0%
Stocking Period: 3 Day
Contact: Tony Cao

Zhejiang Hangyu API Co., Ltd
China
Product Name: 4-(3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-PHENOL
Price: ￥Inquiry/1kg
Purity: 99.5%
Stocking Period: Inquiry
Contact: Vinnie

Henan Tianfu Chemical Co., Ltd.
China
Product Name: TIANFU CHEM 4-(3,7-DIMETHYL-3-VINYL-OCTA-1,6-DIENYL)-PHENOL
Price: $Inquiry/1kg $Inquiry/25kg $Inquiry/1000kg $Inquiry/10ton
Purity: 99.0%
Stocking Period: Inquiry
Contact: Anson

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Bakuchiol

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